Acetone → HCID 18413325, compound

HRID 992774Notes

Reaction equation

HRID 992774 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[CH2:11][CH:10]2[CH2:12][CH:7]1[CH:8]=[CH:9]2.[Mg].O1CCCC1.[Cl-].[NH4+].[CH3:21][C:22]([CH3:24])=[O:23]>>[CH3:21][C:22]([OH:23])([CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[CH2:11][CH:10]2[CH2:12][CH:7]1[CH:8]=[CH:9]2)[CH3:24]

Participants

6

Reactant 5

HCID 180AcetoneHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 18676488HCID 18676488, compound

Product 1

HCID 18413325HCID 18413325, compoundYield 87%

Procedure

A Grignard reagent was prepared from 95.5 g of 1-chloro-4-(5-norbornen-2-yl)butane, 13.3 g of magnesium, and 200 ml of anhydrous tetrahydrofuran. Then, under an atmosphere of nitrogen, 35.5 g of acetone was added thereto at 40° C. over a period of 1 hour. After this mixture was stirred for 1 hour, the reaction product was hydrolyzed by the addition of an aqueous solution of ammonium chloride, followed by separation into aqueous and organic phases. Subsequently, the organic phase was washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by vacuum distillation to obtain 90.5 g of 2-methyl-6-(5-norbornen-2-yl)hexan-2-ol (boiling point: 93-98° C./66 Pa; yield: 87%).

Workup

  1. customfollowed by separation into aqueous and organic phases
  2. washSubsequently, the organic phase was washed with water
  3. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. distillationThe resulting residue was purified by vacuum distillation

Sources & evidence

ORD record
ord-b576ca48d5b44ba7b3574883b2ea4edf
Source dataset
uspto-grants-2002_10
Patent number
US06469220B2

Reaction notes

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